Holding Out Hope
by Lady Eliza
Summary: Trory: Dean has always been in love with Rory Gilmore and assumed she would eventually come back to him, but she has moved on with her blond haired blue eyed love of her life. Story seen through Dean’s eyes. ONE SHOT


**Title: Holding Out Hope**

**Author: **Lady Eliza

**Characters: **All Characters

**Rating:** T

**Summary: **Trory: Dean has always been in love with Rory Gilmore and assumed she would eventually come back to him, but she has moved on with her blond haired blue eyed love of her life. Story seen through Dean's eyes. ONE SHOT

**Disclaimer: **I do not own Gilmore Girls or any of its characters.

**AN:** Hello everyone this is my second fanfic, but my first Trory. I am the author of 'Life and Times of a Socialite' it's a Rogan. I hope to hear your opinions of thisfic,I hope I have portrayed the characters well. Please Review.

**Dedication:** This is dedicated to **Vivilp182, **who had wanted Tristan in my other fic but I couldn't fit him in. Vivi I hope you like this and can't wait to hear what you think of this fic.

Dean Forrester hadn't thought about his first love in a many number of years. Yes, she had occasionally invaded his mind when he was reminiscing about the past and the good times, but that had been it.

He was currently working as a mailroom clerk at a prestigious banking firm in New York City. The same family had run the company for ten generations so they were basically descendents of old money. Dean was still single, even though he and Lindsay had been divorced for six years now. He had made a vow that he wouldn't marry again until he dated the girl for at least a year.

Dean had left Stars Hollow right after the departure of one Rory Gilmore. He felt like a criminal after the town had found out about his affair with Rory. She had come out of the affair unscathed, which had left him to feel the brunt of the blame. Dean had felt as though he was being suffocated from all the negative criticism, so one day he had packed his bags and left good ole' Stars Hollow behind. And he hadn't looked back ever since.

After six years in the big apple he thought he had a good life, though his parents would beg to differ. He didn't know what their problem was; he had a nice apartment, food on his table, and an okay social life. He'd never had big plans for his life the way Rory did, so he was happy with what he had, and didn't bother trying to strive for things he knew he couldn't achieve.

Dean was a little curious as to the reason he was thinking about Rory. She would always have a special part in his heart and he would always love her, but there was no reason to think about her for no apparent reason. He just shrugged it off.

Dean got ready for work like he did everyday. He got into his uniform, which consisted of khakis and a blue dress shirt. He ate breakfast and caught the 7:30 train to work. It was his normal routine and he didn't like breaking it.

The moment he stepped into the mailroom there was a buzz of activity. He didn't get it, it seemed like a normal Thursday to him. He found out the reason when he went to his work area and Ernie, his neighbour and friend filled him in. "Deano, how's is going? Did you here the gossip? Apparently the boss is here for an impromptu check-up. Got everyone buzzing like little working bees."

"The boss….I thought he was based in the London offices. What's he doing here in New York without fair warning?" asked Dean.

"It seems he's finally going to take over for his old man here in New York. Even though his dad has been semi-retired and handed over the reigns of the business to the son, he, the dad, was still in charge of the New York offices. I heard, through the grapevine of course, that the boss man bought a big ole' penthouse on Fifth Avenue," said Ernie.

"Ernie your just full of information aren't you," said Dean sarcastically.

"Hey, I just caught you up on the office gossip, don't give me lip," joked Ernie.

"So, do we know the reason for this sudden change?" asked Dean.

"Who knows? _Rich people_, isn't it what they do, move to a different locale the minute they start getting bored. Besides we have a staff meeting at the end of the day where all the employees have to show up so I'm sure they'll explain it to us then," said Ernie. Dean just nodded his head and got right down to work.

Dean was eating lunch in the employee cafeteria when he felt a little tug on his pants. He looked down and noticed an adorable little girl. She had blond hair, the most peculiar blue eyes, and looked to be around three years old. He bent down to her level and asked, "Hello, are you lost?"

"Hmm…nope I'm just looking around this place. I'm Isabella, but everyone calls me Bella. What's your name?" asked the little munchkin.

Dean laughed out loud. The little girl seemed so mature for her age. "I'm Dean Forrester and I work here. Now aren't your mom and dad going to be worried about you?"

"Oh no, they know exactly where I am. So how do you like working here?" asked Bella.

Dean sat back in his chair and invited Bella to take a seat across from him. She sat down crossed her legs and folded her hands on her lap. She looked like a proper lady and she was waiting for him to answer her question. Dean indulged her, "I don't mind working here it's nice. So why are you here? Does you mom or dad work here?" asked Dean.

"I'm here with my parents. My mommy and daddy told me I could look around, but I wasn't supposed to go too far. So how come you're eating by yourself?" asked Bella.

"My friends decided to buy their lunches today, but I had brought mine from home and that's why you found me eating lunch alone today," said Dean.

"Oh I see, so do you have a favourite book?" asked Bella.

"Not at the moment, what about you?"

"I love Pride and Prejudice so much. I was Elizabeth Bennet for Halloween. My Granny made me the outfit and sent it over to me."

"Well, that was nice of your Granny."

"What's your favourite colour?"

"Blue."

"Do you have any kids like me?"

"No, I'm not married. You ask a lot of questions."

"My daddy says the exact same thing. He says I sound like my great-Granny, who is a gossipmonger."

Dean burst out laughing at that. This little girl seemed bright and energetic and full of questions. He had no idea why she chose to talk to him, but he was enjoying this conversation immensely more so than some adults.

He looked at his watch and realized that lunch was over. "Well Bella, it was nice talking to you but I have to get back to work. I'm sure I'll run into you again."

"Bye Dean," then she was off and running.

Dean thought nothing of the little girl until he was standing in a line to welcome the boss and she came running in. She looked at all the people in line and zeroed in on him. "Hi Dean."

"Hi Bella, what are you doing down here?" asked Dean.

"I came with my daddy, so this is where you work huh?"

Before Dean could reply the little girl sprinted back outside when someone called her name. Ernie gave him a weird look since it wasn't everyday a little girl greeted him by name. There was a flurry of activity and a tall man with sun streaked blond hair came bounding through the door. The man looked like he belonged on the cover of GQ. Ernie nudged him and said, "That's the boss: Tristan DuGrey."

'_Now why did that name seem so familiar to him?'_ It would eventually come back to him, but he couldn't help being frustrated since it was going to bother him until he remembered. He listened to Mr. DuGrey greet the managers, then check out the workstations, and finally make a speech about teamwork. Visits such as these were used to boost the morale of the employees since they felt the big brass upstairs forgot about them, which was true in most cases.

Dean listened to the speech with half an ear. He looked around for Bella and found her near the doorway with a nicely dressed brown haired woman. The woman's face was turned in the opposite direction so Dean didn't get a good look at it. When she did turn around Dean forgot to breathe.

The woman looked like Rory Gilmore, but what would Rory be doing here at DuGrey Enterprises. Rory was a journalist she wouldn't be here, but then again it definitely looked like her. He decided that whatever newspaper she was working for wanted to cover the return of the CEO of DuGrey Enterprises.

As Dean watched, Rory spoke to Bella then disappeared down the hallway. Dean felt like he had travelled back in time because with just one look at Rory's face he was sixteen years old all over again. He hadn't noticed it but the boss had left and everyone was back at work. He followed their example and did the same.

Dean was taking his half hour break by sitting in the cafeteria drinking coffee and thinking about Rory when Bella approached him again. She sat down before she began to talk, "Hi again."

"Hello Bella, how has your day been so far?" asked Dean.

"Oh I love it. I can't wait to be CEO of this company."

Dean laughed at the child's attempt at humour, "Well it'll take you a while to be up there with the bosses, but the CEO has to be part of the family that owns this firm," explained Dean.

"Oh I know that silly, but I will one day be CEO of this company," the child firmly.

"Alright, I believe you," consoled Dean.

"You don't believe me do you? Here have my card and look out for me since I will be your boss," said Bella then she took out a white business card out of her jacket pocket and handed it to him.

Dean was amused since this was the first child he'd ever met who'd given him a business card. He hadn't realized that times had changed so much; a little girl was acting so grown up instead of playing with her doll.

He read the card then put his coffee down quickly. It read: Isabella L.G. DuGrey IV and had a cell phone number where the lady could be reached. He was stunned into silence since he was in fact talking to the future CEO of DuGrey Enterprises.

"Your Tristan DuGrey's daughter?" asked Dean.

"Yep."

"So I guess you will be the future CEO of the company huh?"

"I told you."

Dean chuckled and shook his head. He hadn't realized exactly whom he had been talking to when Bella started chatting with him. He was about to reply when a pager when off. He watched in fascination and shock as she unclipped a pager from her pant loop and look at the number, then give him an annoyed look.

"Parents," Bella said in an exasperating manner.

Dean just chuckled then stopped and asked her the question that had been plaguing him since he saw her in the mailroom. "Bella, was the woman you were talking to in the doorway of the mailroom Rory Gilmore, the journalist?"

Bella was standing by now, but she turned to face him when he asked her the question. "Yeah that was Rory Gilmore, but no one calls her that anymore," said Bella.

"Oh and why not? What do _you_ call her?" teased Dean.

"She's known as Rory DuGrey now and I call her mommy. Bye," said Bella. She turned around and strode out of the cafeteria with a purpose.

Dean was dumbstruck. He couldn't believe he had been talking to Rory's daughter this whole time. He knew Bella's eyes looked familiar and now the name Tristan DuGrey came back to him as well. _Rory and 'the accountant'?_ Dean could just sit there like an idiot and watch his coffee grow cold.

After his conversation with Bella, Dean couldn't think about anything but Rory Gilmore, or DuGrey now. He'd had no idea she'd gotten married and that she had had kids. But that shouldn't have surprised him since Rory would not have let anything stand in her way of marriage and kids. Her grandmother was probably ecstatic that Rory was married to a DuGrey.

Dean wondered if the marriage was based on love or a business arrangement, he didn't want to think about Rory actually wanting to marry the accountant. He busied himself with work and tried not think about Rory, Bella, or Tristan DuGrey. Dean couldn't believe the irony of the situation, he was working for the accountant, while Rory was married to the cocky S.O.B.

He hadn't been back in Stars Hollow in three years, but wouldn't his parents have told him Rory was married? Or had kids? Probably not, he tried avoiding going home at all costs. His sister Clara told him about Lorelai getting married to Luke and how they were expecting a child in the fall, but she never mentioned Rory attending the wedding.

Dean had no idea why Rory had left Stars Hollow and moved to Europe, some people had said her great-grandmother had willed Rory the house in London and she wanted to live there for a while. But no one, except for Luke and Lorelai, knew why the town's princess had up and left.

He would have to see her soon enough, since there was going to be a staff meeting of some kind where the employees would meet Tristan DuGrey and his family. Dean didn't want to see Rory happy with her young family. In the back of his mind Dean had been holding out hope that Rory would eventually come back to him and they would both live happily ever after. She was _it _for him and he was upset that she had married and had kids with a man like Tristan DuGrey.

Dean walked into the large auditorium that hosted many a conferences for DuGrey Enterprises since it had been built twenty years ago. He sat down towards the middle where Ernie had saved him a seat. "Deano, glad your here. Hope this thing finishes fast so we can have our weekly poker game. You know how the wife gets when I don't make it in time for supper. The woman can be brutal," Ernie actually shuddered.

Dean laughed, "Yeah I hope Mary Ellen doesn't beat you with a stick like the last time. How long did it take you to get rid of the bruises?"

"I now, regret telling you about that incident. Remember it's between you, me and the wife," said Ernie, which earned a chuckle from Dean.

Ernie O'Brien was a perceptive man and he knew that Dean held a whole many secrets. He had never divulged anything to him even though they had been friends for four years. Ernie respected and admired Dean and his work ethic. They had a weekly poker game going with some of the guys from the mailroom, which took place every Thursday after work at Dean's place. Dean had become a permanent fixture in the O'Brien household and Ernie's kids thought the world of him. Mrs. O'Brien treated Dean like another one of her children and she was forever setting him up on blind dates trying to find him the perfect spouse.

Ernie had told his wife, quite astutely, that young Dean had gotten burned by a woman in his past and couldn't get over the heartbreak. Dean was never in a relationship for too long and he never spoke of his past with anyone. Heck, he hardly ever went back home to visit his folks or his sisters. Ernie who was a private man himself had decided to leave well enough alone and let bygones be bygones. He wasn't going to pry in another man's affairs if the man did not want to divulge the information himself.

"So what do you think we're going to learn at this meeting that we won't find if we google the boss and his wife?" asked Ernie.

"You got me Ernie," said Dean.

"So, tell me who was that little toe head you were talking to when the boss came to visit?" asked Ernie.

"You won't believe me if I told you," said Dean.

"Now you gotta tell me."

"The little girl came and talked to me when I was eating my lunch, then again in the mailroom, she said was here with her mommy and daddy. Guess who she is?"

"I'm not a damn mind reader, get on with it."

"The toe head happens to be Isabella DuGrey, our future boss."

"Ah shit. I didn't even make an impression on her. Just my luck that our future CEO comes to the mailroom and I have no idea who she is," said Ernie.

Dean just shook his head and looked toward the podium. He watched with jealous eyes when Rory walked up with Tristan, Isabella, and a baby in her arms. They made the perfect family and Tristan DuGrey looked like the happiest man in the world with his three women. Dean wanted to shout at the injustice of it all, _'how does a cocky bastard like Tristan DuGrey have it all?'_

He watched as Rory held the baby, he couldn't tell if it was a boy or girl from this far, that was supposed to be his child not the 'accountant's.' Dean was seething inside since he had to watch a life with Rory go up in smoke. Dean watched as an older version of Tristan kiss Rory, Bella, and the baby then shake hands with Tristan, so this was Alistair DuGrey, Tristan's father.

Alistair came up to the microphone and started talking about the new chapter of the company's life and he introduced his family. Dean smiled at the part where the proud grandfather spoke about the future of DuGrey Enterprises and pointed to Bella who waved like she was the queen. But Dean was not happy to see Tristan have his hand around Rory and whisper to her throughout the entire speech.

When Tristan came up the mike the entire family came with him. "Hello everyone, I am Tristan DuGrey, this is my wife Rory and my daughters Isabella and Lorelai. I am happy to be back in the states and taking over the New York headquarters, which has always been the heart of the company. My family and I want to put you at ease during this time of change. Nothing is going to change except me walking around the building and the occasional surprise visits by our future CEO, Bella."

Dean laughed at the last part but he tuned out the rest of the long speech that seemed like it wouldn't end. Today, he had watched a secret fantasy of his go up in smoke and he wanted to go home and lick his wounds. He didn't know if he could work for DuGrey Enterprises anymore after finding out that Rory was married to his boss.

He watched as Rory and the children sat down beside Alistair DuGrey.

Rory watched her husband proudly as he gave his speech. She had married a wonderful man and he and the children were the most important things in her life. Rory was glad that they were back in the states and it was lovely having family nearby so the kids could spend time with everyone on a day-to-day basis instead of only on vacations and holidays.

She looked out into the crowd and watched as many of the employees get caught up in her husband's magnetism and charismatic personality. She knew their eldest daughter, Isabella, had her father's personality, her mother's drive, her grandmother's sense of adventure, and both her great-great grandmothers' need for gossip. Rory looked down at the little baby that was in her arms and knew she had another firecracker on her hands. Lorelai Gilmore DuGrey IV was going to be a handful should she inherit any aspects of her sisters personality or temperament.

Rory was still looking in the crowd when she thought she saw Dean in the audience, but that couldn't be. She hadn't seen or heard from Dean in ages. She actually forgot all about him and last she heard he and Lindsay had gotten a divorce then went their separate ways. Rory was trying to get a glimpse of the Dean-look-alike when her father-in-law, Alistair asked her a question, "I sorry dad, what did you say?"

"Daydreaming Rory? I asked if you wanted me to hold Lorelai for a while?" said Alistair affectionately.

"Sure, that would be great, dad," said Rory.

Alistair was like any grandfather and he held his little granddaughter like she was a precious jewel. He had been so happy when Rory and Tristan had announced their plans to wed. When their first child was born he had been in such high spirits that he gave everyone at work a raise, which showed you how happy he was about the birth of his first grandchild. He was finally going to be able to retire and spend some quality time with his grandchildren as well as improve his golf game so he could beat Richard Gilmore. They had a friendly rivalry going on.

Rory was still trying to find the familiar face in the crowd to see if it was in fact him, but her husband finished his speech and now the Chairman of the Board was speaking to the employees. Tristan bent down to give her kiss and she forgot about Dean. The man could kiss and she ended it before it got out of hand, in a public venue no less. She heard Alistair discreetly cough to cover up his laughter.

Tristan smirked at her and said, "So how was I? Do you think they felt comfortable around me?"

"Yes, I think you did really well sweetie," said Rory.

"Thank you wife of mine," said Tristan in a cocky manner.

Rory just rolled her eyes and tried to listen to the Chairman speak, but her daughter who craved attention just like her father interrupted. "Daddy I thought you did good. Do you think, as the future CEO of this company, I should make as speech as well?" asked Bella.

Rory and Alistair tried not to laugh out loud at the notion of little Bella making a speech to the entire employee population; it was a funny image. But Tristan who thought the world of both his daughters answered her question as if she were an adult. "Bella, I don't think it would be appropriate for you to make such a speech at this moment, but maybe in the future you may," said Tristan.

She smiled the same smile that made him fall in love with her mother and he melted. "Okay daddy," said the mature Bella.

Tristan peeked over his wife's shoulder to see the sleeping form of his youngest child Lorelai. He was still a little shocked at how his girls had both sets of grandparents and great-grandparents wrapped around their little fingers. Tristan knew he spoiled them and gave them just about anything when they asked for it, but they could even work Luke who was not known for liking kids or indulging them. But then again they were Gilmore girls so he shouldn't worry.

When Tristan and Rory had first started dating they didn't know what kind of a relationship they would have. Tristan had to convince Rory that he had changed and he had to show her through his actions. The two of them had no expectations whatsoever going into the relationship but had gained so much. They were married after only six months of dating and had waited a year before starting a family. He was extremely happy in his marriage and doted on his daughters. Rory and Tristan had decided together that it was about time that they moved back to the States, and New York to be exact.

Tristan watched his wife for a while and she seemed distracted, "Rory is everything okay?"

Rory turned to her husband and said, "Yeah everything is fine Tris. I just thought I saw someone I recognized, but I guess I was just imagining it."

Dean was simmering with Jealousy since Rory looked to be happy with her husband and 1.5 kids. He couldn't believe Rory had married into a high society family. Even though she belonged to a prominent family, Dean had always assumed she had some sense and would marry a normal guy. But it seemed like she married a man Emily Gilmore would be proud to call grandson.

He had observed some private moments between the couple and he hated to admit it but they seemed genuinely happy together. So there went his idea about the couple's marriage being a business arrangement between the two families. He should've known that Rory would do things her way and please her family at the same time.

Dean had had to watch as Tristan bent over to kiss his wife, a little too long in his opinion, and then speak with his adorable daughter. _Dammit _that ass didn't deserve a wife and family like Rory and her kids. He wished he didn't have to watch the scene play out before him.

He doubted that Rory even noticed him or remembered him for that matter. When the people around him were getting up to leave was when Dean noticed that the meeting had adjourned so stood up to leave as well.

"Deano, we'll meet you at your place in a few alright?" yelled Ernie from the exit.

Dean just nodded his head and went to pick up his things from his desk in the mailroom. As he made his way out of the building he noticed a chauffeured Rolls Royce pull up on the street. He was walking down the stairs and noticed Bella run to the chauffeur and chat with him. He was about to go and say hi to her, but it was then he noticed her father Tristan and grandfather Alistair were also coming out of the building from the east side and a few paces behind them was Rory with little Lorelai in her arms.

Dean couldn't help but stare at the woman who had bewitched his life since the first time she had appeared in it. He didn't think there would be another woman that he would love as much as he loved Rory. God, he wished things could be different. He wished the two little girls were his instead of the accountants.

He could only watch with bitter longing as the young family got into their Rolls Royce and wave to Alistair DuGrey who stood on the pavement and smiled proudly. He would always pine for the girl that was never meant to be a part of his life. He could only watch with cold eyes as Tristan leaned over and kissed his wife for far too long and the car moved into traffic.

Bella saw him on the stairs and she waved to him furiously from within the car. Her eyes lit up just like her mother's and Dean knew then and there that he wouldn't be returning to DuGrey Enterprises ever again. It would be too difficult and there was the off chance he could run into Rory.

He watched the car for a moment longer as it was headed to a penthouse on the Upper East Side that would be the base for the DuGrey family. He quickly turned around and ran to catch the bus and never looked back.

**AN: Please, Please, Please Review.**


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